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Never Duck the Tough Questions

This interview with Dawn Lepore, chairwoman and chief executive of Drugstore.com, was conducted and condensed byAdam Bryant. Ms. Lepore is also a director of eBay and The New York Times Company.

Q.Do you remember the first time you were somebody’s boss?

A. I was hired at Schwab in 1983 to be the manager of the information center. The person who wanted the job was way more technical than me, and that was the reason he didn’t get the job. He was in love with the technology — I wasn’t. He was not happy about having me come in over him. And he said, O.K., you’re so smart — let’s see you do it.

Those were the days when the computers were shipped in, and they were not all put together. So you’d get these little chips, and you have to put them in the motherboard. And so he said, “Well, there’s a shipment here for you.”

So I go to the dock and there are all these boxes with computers in them. I put together 30 computers. After the guy saw me do that, at least I had a little bit of his respect, and we went on to have an O.K. relationship.

A. Every time you take on a new role, building credibility is incredibly important. I don’t think you do it by being smarter than everybody else or knowing more necessarily than everybody else. I think you do it by rolling up your sleeves, by showing commitment, by proving that you’re willing to learn, by asking for help.

All those things earn you credibility, especially if the people who work for you feel like you’re not going to sit back and take credit for what they do, and if they get a sense that you’re going to support them, help them grow.

Q.Other key moments like that?

A. My biggest promotion was moving into the head technology role at Schwab. It’s an important job at Schwab; it reports to the C.E.O. I was 39, and it was very unusual to be a woman running technology. I remember the person who promoted me said that he had several board members call him and say: “Why did you do that? That was a really dumb decision, putting a woman in charge of technology.”

Q.Just because you were a woman?

A. There were no women C.I.O.’s back then. And I don’t have an M.B.A.; I didn’t have a computer science degree. I have a music major. It’s a very unusual profile to be in that position. The reason I got the job was that I took on really tough assignments, things nobody wanted, things that people thought were kind of impossible or thankless tasks. So I proved that I could take on things I didn’t know, and learn. I was willing to take risks, and I’ve always been a good synthesizer. And I was good at building relationships across the company.

Q.So how did the transition go?

A. The first year or 18 months were rough. I found out later that people were calling me the Ice Queen. And I was devastated. But it’s because I felt like I had to be perfect — I couldn’t show any vulnerability.

I had a boss at the time who called me and said: “You know, I really believe in you. I gave you this job, I want you in this job, I really believe in you. You have to get better, though. You have to hire a coach, you have to improve, here are the things you have to do.”

But just having him tell me, I really believe in you, I want you in this job, it made me relax. It was like, O.K., I’m not going to get fired. He’s going to give me a chance to learn on the job and so now I’m going to be a little bit more open and be willing to ask for help.

Q.What other feedback did you get?

A. So, I’m incredibly intuitive. As the technology was evolving and the business was evolving, it was very intuitive to me what we needed to do. But I was not very good about putting that into words. And so people wanted to know, where are we going? And I was absolutely convinced that it was going to be fine and we were going to figure it out.

I’m very comfortable with ambiguity. But when you’re leading a large organization, people are not as comfortable with ambiguity and they want you to be clearer about what’s happening, where you’re taking them. So I had to get better at communicating what I was thinking.

Photo

“You have to be transparent as a leader and you have to be willing to take criticism openly,” says Dawn Lepore, the chairwoman and C.E.O. of Drugstore.com. She is also a director of eBay and The New York Times Company.Credit
Tony Cenicola/The New York Times

We went through a big organizational change, too. We had to lay some people off, we changed the skills, we did a whole skills review because this was moving from old technology to new technology. And so the morale got pretty low. And I would have employee meetings, and they could give me questions anonymously, and I promised them I would read them and answer any question. And there were some pretty ugly questions, like, “Who do you think you are to lead?”

I read every one, and I answered every one, and I stood up in front of the whole group and I did it. So I think over time, they saw I wasn’t going away, I was going to stick, and then we started to get big wins. Getting some wins always helps you as a leader.

Q.That was a risky step to answer those anonymous questions.

A. I’ve always felt that you have to be transparent as a leader and that you have to be willing to take criticism openly. The worst thing you can do is have people with stuff on their minds that they won’t tell you. I think that’s the kiss of death as a leader. And if you’re leading an organization, you want people’s energy going into the competition, solving big problems; you don’t want it going to what’s bothering them inside.

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And people make assumptions — they see little pieces of data and they put something together and they come up with one and one equals six. They don’t have the context. And nine times out of 10, if somebody asks you the question and you give them the context they say, “Oh, now I understand why you did what you did.”

Q. What were the most important leadership lessons for you?

A. My strong beliefs are about commitment, loyalty and taking on hard things. And I’m not quite sure where that came from. When I majored in music in college, I still remember people telling me I wasn’t really talented enough to major in music. But there was a piece of me that just felt like, if you tell me I can’t do something, that’s what I want to go do. And I had to work three times as hard as anybody else, and practice three times as long, just to be able to give the same recital that somebody else was able to give. It’s really important to me to take on things that I thought I couldn’t do and prove to myself and to others that I could do them.

Q. Any bosses you had who were big influences?

A. I had a very bad boss early in my career. She was older than I was. She’d started in the financial services industry and she’d had a very hard time, so I think that probably shaped her as a leader. She was very smart but had terrible communication skills. She did not make people feel valued or comfortable or like they were supported at all. And I remember what that felt like. And I thought, I’m never going to do that to people.

Q.How long did you work for her?

A. Many years. I almost left twice.

Q.What’s your advice to people stuck working for a bad boss?

A. Life is about trade-offs. And you have to be conscious of the trade-off you’re making. I felt there were enough other positives in the environment and enough opportunity that I stuck it out. But, you know, I was unhappy. I had to kind of just take a deep breath and say, O.K., I know this is going to end and I’m willing to put up with this.

But you can’t be a victim. If you let yourself become a victim, that’s the kiss of death. So you’ve got to feel, O.K., I am choosing to do this, and when I decide I can no longer do it, then I will take action. So I will not let myself be so belittled that I think I can’t do anything. If it starts undermining your confidence, then you have to leave, because then that seeps into everything you do.

Q. Who else influenced your leadership style?

A. When I became the C.I.O. at Schwab, I had the benefit of being able to interact with a lot of technology C.E.O.’s, because they would come to sell to me. So I got to meet with Scott McNealy, Bill Gates, Steve Ballmer, John Chambers and others. And I would always say to them, let’s talk about your product, but I’d really love to hear more about your company, your culture, your leadership. So I really picked their brains.

I learned something from every single one of them. And I’ve served on a bunch of different boards, and I’ve had an opportunity to just learn from the C.E.O. of the company as well as all the other board members.

Q. Let’s talk about hiring.

A. I’m a very intuitive interviewer, so I want to get to know people. I always ask them to tell me their background. I can read it on the résumé, but I always want them to describe their background to me, because it’s interesting to see what people choose to tell you about themselves, how they describe the moves they’ve made, the changes they’ve made.

I’m looking for intellect, I’m looking for experience level, I’m looking for cultural fit, which is hard to describe. It’s more of a soft thing. And then I am looking for this whole commitment thing. Are they willing to stick it out during hard things? How have they handled setbacks? How have they handled tough times? If you ask them about things they’re most proud of, are they things they’ve done themselves or are they things where they’ve helped a team do more than they ever thought they could?

Q. Anything unusual about the way you run meetings?

A. We have a little joke where I’ll tell people, a light bulb or a gun. A light bulb means this is just an idea I had, so think about it, see if you think it’s a good one. Either follow up or don’t, but it’s just an idea. A gun is, I want you to do this. People don’t always know if you mean something as just as an idea, or you want them to go do it.

This is a more complete version of the story than the one that appeared in print.

A version of this interview appears in print on July 18, 2010, on Page BU2 of the New York edition with the headline: Never Duck the Tough Questions. Order Reprints|Today's Paper|Subscribe